Prevention of deterioration of cotton cord by heat



Patented Aug. 4, 1936 PREVENTION OF ADETERIORATION F COTTON CORD BY HEAT Lorin B. sebrellySilver Lake; Ohio, assignor to Wingfoot. Corporation, Wilmington, Del., a

co poration of Delaware includes the process of trea treated cords.

It has been observed heretofore that cords and threads, especially those ton fibers, exhibit under X-rays a de finite ,pattern associated with the molecularstructure ot the cotton. When subjected to relatively high temperatures, for example, 250 degrees F.', a' molecular rearrangement occurs which" causes the pattern to disappear, such rearrangement beingaccompanied by premature loss of strength and resultant failure of the cord application of relatively small tensional forces. Upon cooling, the major portion of the original strength is regained.

This loss of strength at relatively hightemperatures is particularly objectionable in cords employed in the construction because much heat is developed in the latter when run at high speeds.

tires, the temperatures sometimes reach values in excess of 250 degrees F. As a result, the cords of which the tire carcasses which normally are the principal tension resisting elements in the tire are so weakened that premature ruptures'or blowout's tend to occur. My invention resides in the discovery that ordinary cotton cords, threads, filaments, etc.,

when treated with reagents No Drawing. Application March 1, 1932, Serial No. 596,146 Y 14 Claims. (or. 8-20) ting cords and the prepared from cot- ,tioned. or thread 111 0 1 Aniline of pneumatic tires,

In truck and bus are composed and of the type herein' pattern at temperatures materially above that at which the patternnormally vanishes. treated cords possess substantially greater tensilestrength at ordinary temperatures and retain their original tensile strength when subjected to relatively high temperatures materially better than ordinary untreated cord. Although numerous reagents have been found more or less effective in retarding or resisting the action of relatively high temperatures in cords, I 10 have established experimentally that certain organic compounds, particularly the amines, are

especially satisfactory in this respect. v

The following are some of the amines which I have foundto be suitable forthe purposes men- 15 Such 2 4-diamino diphenyl amine o-toluidine Di-methyl u-naphthylamine Cycle hexyl amine a and fl-naphthylamine 4-amino m-xylene m-toluylene diamine Di-n-propylamine Di-iso-amyl amine Thio phenyl fl-naphthylamin Di-butyl amine Piperidine Di-ethyl amine Allyl amine Butyl amine The results obtained with these compounds are descnbed, continue to produce a definite X-ray summarized in the following table: 35

Tensiles of treated Tensiles of raw cord cord Chemical Chemical treatment 250 F. F. 2 50 F 75 F. 40

Aniline- (a) 3 hrs. in aniline at 120 0.. 7 l2. 7 19. 0 10. 1 17. 2 (b) 3 hrs. in aniline at"120 0., drained, 1?. 7 1i). 0 l0. 1 17. 2

3 hrs. in CS: at 25 C. (c) 3 hrs. in aniline at 120 0., drained, I 11. 9 l9. 1 10. 1 17. 2 3 hrs. in 30% formaldehyde at 0. 45

(d) Heated in aniline to -120" 0., 12.7 20.4 10.4 17. I

allowed to stand 16 hrs. in liquid, 4 washed in ether. 24-diamino diphenyl- 2-4-diamino diphenyl amine under 11.3 17. 5 10. 1 17.2

amine. 7-1 600 lbs. pressure. o-tolnidine Heated inmoluidine tons near 110- 13.0 20. 5 10.4 17:1

C. as ssible, allowed to stand 16 hrs. in liquid, washed in ether. 50 Di-methyl u-naphthyl- 2% hrs. in di-methyl a-naphthylamine 11.8 18.6 10.4 17. l

mine. at 70 0., allowed to stand in solution over night. r Cyclo beryl amine (41) .2 hrs. in cyclo hexyl amine at 13.3 21.0 10.4 17.1-

(b) 3 hrs. in cycle hexyl amine at 12.8 20.8

Tensiles of treated Tenslles of raw cord cord Chemical Chemical treatment 250 F. 75 F. 250' F. 75 F B-naphthy1-amine Heated 60 gms. B-naphthylamine in 12.5 20.2 a 10.4 17.1

350 cc. xylene and 25 cc. C H; to as near -120 C. as possible allowed to hstand 15 hrs. inliquid, washed in et er. m-toluylene diamiue. Heated 50 gms. m-toluylene diamine 13.2 20.7 10.4 17.1

in 75 cc. xylcncand 350 cc. toluene to as near 110120 C. as possible, allowed to stand 15% hrs.,washed in ct er. Di-n-propyl amino 2% hrs. in di-n-propyl amine at 70 12.6 20.1 10.4 17 1 C.,hallowed to stand in liquid over nig t. Di-iso-amyl amine 2% hrs. in di-iso-amyl amineat 70 12.0 19.6 10.4 17 1 0 atllowed to stand in liquid over nlg Thio phenyl fl-naphthyl 22 hrs. in thio phenyl B-naphthylamine 11.2 18. 0 10. 7 17. 5

a 1:18. in benzol at room temperature. Di-butyl amine (a) 2 hrs. in 100% dibutylamine at 10.7 17.5 10.5 18. 1

220 5., 2 hrs. in crotonaldehyde at 240 (b) 3 lirs. in 100% dibutylamine at 12.3 20.6 10.5 18.1

162 (cg-A3 hlr s. in 100% dibutylamine at 12.3 19. 8 10. 5 18. 1

0 I (d) 3 hrs. in 100% dibutylamine at 10. 7 19. 7 10.5 18. 1

F., 3 hrs. in 10% triethanolamlne in water at 210 F. (e) 3 hrs. in 100% dibutylamine at 10. 3 18. 7 l0. 5 18 1 162 F., 3 hrs. in 10% triethanol amine in water at 202 F. (f) 3 hrs. in 100% dibutylamine at 10. 7 20. 3 10.5 18 1 I 3 hrs. in 2.1% triethanol amine in water at 204 F. (a) 3 hrs. in 100% dibutylomine at 10. 7 19.0 10. 5 18 1 162 F., 3 hrs. in 20% triethanol mine in water at 204 F. (ll) 3 hrs. in 100% dibutylamine at 11.7 10.8

198 l 1% hrs. in 20% furiuraldehyde in alcohol at 174 F. (i) 3 hrs. in 100% dibutylamine at 198 11. 1 10.8

F., 1% hrs. in 20% heptaldehyde in alcohol at 174 F. (j)F3 hrs. in 100% dibutylamine at 218 12. 0 10. 8 (k) 3 hrs. in 100% dibutylamine at 218 11. 3 10. 8

F., 3 hrs. in 20% crotonaldehyde in alcohol at 172 F. Piperidine... (a) 2% hrs. in piperidine at 75 0., al- 13. 6 20.4 10.4 17.1

'lowed to stand in liquid over night. (b) 3 hrs. in 100% piperldine at 212 F., 12. 1 10.8

1 hrs. in 20% lurluraldehyde in a cohol at 174 -F. (c) 3 hrs. in 100% piperidine at 212 F., 11. 5 10.8

3 hrs. in 20% heptaldehyde in alcohol at 174 F. (d; 3 hrs. in 100% piperidine at 212 F. 12. 3 10.8 (a 3 hrs. in 21% diethylamine in 10. 1 17. 3 l0. 1 17. 2

water at room temperature. (0) 3 hrs. in 21% diethylamine in 11.7 18.2 10.1 17. 2

water at 75 (c) 3 hrs. in 85% diethylamine in 12.8 19. 2 10. 1 17. 2

water at 65 C. (d) Cord exhausted under vacuum of 12. 3 18.3 10. 1 17. 2

. water pump, 85% diethylamlne adheated to boiling, 3 hrs. at

(e) 3 hrs. in 85% diethylamine at 65 12. 6 19. 6 10. 1 17.2

530.; 8 hrs. in 30% formaldehyde at 2% hrs. in allyl mine at 70C., al- 10.4 17. 1 lowed to stand in liquid over night. Butyl amine (a): 11 n 50% butylamine in water 10. 7 17.5

8 1 (b) 3 hrs. in 1(Xl% butylamino at 158 F 10. 7 17. 5 (c) 3 hrs. in 100% butylamine at 162 F. 10. 7 17. 5 (d) 72 hrs. in 100% butylamine at 72 F- 10. 5 18. l (0) 3 hrs. in 100% butylamino at 10. 7 17. 5

F., washod'in water. (I) 15 mins. in 15% butylamine in 10. 7 17. 5 water at 111 F.

In these tests, samples of cord were treated with these reagents, after which one set of samples was tested for tensilestrength at normal or approximately room temperatures and at 34 percent relative humidity. The second set of samples was then subjected to tests identical with those conducted upon the first set, exceptthat the temperature was maintained at a value of 250 degrees F. during the test. The control employed was identical in every respect with the treated cord, except that it was not treated.

From the table, it will be apparent that cords which-have been. treated are materially higher in tensile strength both at relatively high temperatures and at ordinary or normal temperatures.

In some cases, this increase amounts to as much in connection with fabric employed in the manufacture of hose used to convey heated liquids. It

is also tobe understood that the invention is not limited to the specific compounds disclosed herein. All amines tested have been found to be effective to some extent, from which it appears.

probable that all of the compoundsof this class exhibit properties of the kind described.

This application is a continuation in part of my prior application Serial No. 420,638, flied January 13, 1930, for Prevention of deterioration of cotton cord by heat, now abandoned.

Although I have described only the preferred forms which the invention may assume, it will be pparent to those skilled in the art that it is not limited thereto, but that various modifications may-be made without departing from the spirit of the invention or from the scope of the app nded claims, It is intended that the patent shall cover, by suitable expression in the appended claims, whatever features of patentable novelty reside in the invention.

What I claim is: 1. The method of treating cotton which comprises subjecting it to the action of an amine having at least one univalent organic radical attached to the nitrogen atom of the amine as a substituent whereby, without producing any material change in the appearance of the cotton or the way,it feels, it is made to have greater tensile strength at 250 F. than untreated cotton at the same temperature.

2. The method of treating cotton which comprises subjecting it at an elevated temperature to the action of an amine selected from the following group:

' comprises subjecting it to the action of a primary amine wherebywlthout producing any material change in its appearance or the way it-feels the cord is made to have greater tensile strength at 250 the untreated cord at the same temperature.

4. The method of treating a cotton cord'which comprises subjecting it to the action of an allphatic amine whereby without producing any materlal'change in its appearance or the way "it feelsthecordismadetohavegreatcrtensile at the temperature.

strength at 250' 1". than the untreated cord at 7 the same temperature.

5. The method of treating a cotton cord which comprises subjecting it to the action of an allcyclic amine whereby without producing any ma- 5 terial change in its appearance or the way it feels the cord is made to have greater tensile strength at 250 F. than the untreated cord at the same temperature.

8. The method of treating a cotton cord which 10 comprises subjecting it to the action of cyclohexyl amine whereby without producing any material change in its appearance or the way it feels the cord is made to have greater tensile strength at 250 F. than the untreated cord at the same tem- 1 '7. The method of treating a cotton cord which comprises subjecting it to the action. of a primary aliphatic amine whereby without producing any material change in its appearance orthe way it 20 feels the cord is made to have greater tensile strength at 250 I. than the untreated cord'at the same temperatin-e.

8. The method of treating a cotton cord which comprises subjecting it to the action of a butyl 25 amine whereby without producing any material change in its appearance or the way it feels the cord is made to have greater tensile strength at 250 F, than theuntreated cord at tlie same 'temp rature. 9. The method of treating a cotton cord whichcomprises subjecting it to the action of di-butyl amine whereby without producing any material change in its appearance or the way it feels-the cord is made to have greater tensile strength at 35 250 F. than theuntreated cord at the same temperature.

10. The method of treating a cotton cord which comprisessubjecting it to the action of aniline whereby without producing any material change 40 r in its appearance or the way it feels the cord is made to have greater tensile strength at 250 1''. than the untreated cord at the same temperature.

11. A cotton cord treated with an amine, which treated cord has the same general appearance 45 and feels substantially the same as'an untreated cotton cord and has greater tensile strength at 250 F. than the untreated cord at the same tem- 12. A cotton cord treated with aniline, which50 treated cord has the same general appearance and feels substantially the same as an untreated cotton cord and has greater'tensile strength at 250? F. than-the untreated cord atthe same temperature 65 13,1 cotton cord treated with a butyl amine,

.whlchtreatedcordhasthesame general appear-.

ance and feelssubstantially the same as an un- ;t1eated cotton cord and has greater tensile strength at 250 Ethan the untreated cord at the 00 same temperature.

:14. A cotton-cord treated withcycloheni amine, which treatedcord has the same general appearanoeandfeelssubstantiallythe sameasan cotton cord and possesses greater ten- 05 this strengthat 250' Ethan the untreated cord new 3. smasrn 

